Headmaster Punishment Stories

31,842 results
Orientation
Length
Source
Infinite Scroll

First Interlude

by tovesslithy on Sep 14, 2017
BDSM

24 First Interlude Helen Shagton was forty-two years old. Despite this very adult age, she was nursing a very recently and well-caned bottom. She was just returning home by car. However, she had felt, as she so often did, that she really needed a good, hard, school caning style punishment herself. The Headmaster, had, naturally, been very happy to oblige h...

The Weekend at the Lake

by erotiquill on Sep 13, 2017
Erotic Couplings

It was two weeks ago that Ray and Emma first told us about Jon. He was someone they had known for a little over two years and felt that our relationship had reached the point where they could tell us about him. My wife, Gwen, and I have had a sexual relationship with Ray and Emma for almost a year and have become very good friends during that time. "We have...

Celebrate Freedom!

by sophia jane on Sep 16, 2017
Reviews & Essays

Thanks to Softouch911, again, for being a fantastic editor and friend! * My grandmother had a bookmark when I was growing up that said: "Celebrate freedom. Read a banned book." The irony never escaped me; while we have free press, we also have people who exercise their freedoms by protesting, and banning, the words of others. My grandmother celebrated he...

The Red Moon's Power: Hawks Tale 01

by Duzzel on Sep 15, 2017
Sci-Fi & Fantasy

The Red Moon's Power: Hawks Tale OK, so like I said before, It's been way too long. I finally decided on a much needed conclusion on Hawkens story. He needed a happy ending or so I've been told. So here it is. Enjoy! ----------- ~5 years before Shinai and Aiden were reunited and just before the Katsari attack on the Senatri, At Illoris Academy in the Sitr...

The Headmaster Ch. 04

by deadeye_76 on Sep 16, 2017
BDSM

Chapter 4. Christy's Back... with a friend! We hadn't had any action of any kind, which was surprising and I kept mulling over different ways for my wife to get her share of attention. I was thinking about something to do with the Halloween party that was coming up while my wife and I sat in the closet one day when something very interesting happened in the...

The Last Sashay

by mDyne on Sep 15, 2017
BDSM

Chapter 1. Mr. Punire "Good to see you again Mr. Punire. Has it been two years already?" "Two years less a day, according to my calendar. Schools I always do Fridays, and for an old customer like you, always the Friday before spring break." "Still doing a lot of traveling?" "Not so much any more; there aren't too many places where I can learn something t...

Code Name Tequila Ch. 13

by Travel_by_day on Sep 15, 2017
Transsexuals & Crossdressers

"Right here, right now... Right here, right now..." The music boomed out of the Bang and Olufsen stereo system as Carlos followed the Hyundai driven by Fernandez into the outskirts of Colon. Carlos turned the music up. The drive, though scenic, had been boring, and the music made the time pass. Carlos could feel the power of the Audi R8 through the wheel an...

The Party's Ripe for Caning

by lesliejones on Sep 19, 2017
BDSM

It was a most unusual change for the boys in the senior class at Hamilton Hall, an elite high school, when the Headmaster, Mr. Henderson, appeared in their class to introduce them to their new home-room teacher, Miss Linda Crawford. First of all, there had never even been a woman teacher at Hamilton Hall, much less one so young as Miss Crawford, nor did it s...

Mercedes Senior Year at St. Vincent Ch. 02-03

by OTKTop on Aug 28, 2018
BDSM

Chapter 2: Mercedes is aroused from her spanking. (This is more of a story I have written for a submissive friend of mine. She likes to imagine what it could have been like to be spanked at her boarding school. It's only real in that this is what she imagines happening.) Mercedes walked quickly back to her dorm room, her mind clouded with a variety of thou...

Journey of Submission

by msterrilynn on Sep 12, 2017
BDSM

Chapter 1: Phone Call The phone rang as she came in the door with her hands full of groceries. Amelia set them down and reached for the phone. "Hello?" she said. "You have been accepted into The Academy. A packet will soon arrive with instructions on how to proceed", a voice said. Amelia collapsed into a nearby chair and slowly smiled. She has been accepted...